


Momma's Boy

by AgentAlexKrycek



Category: Teen Wolf (TV)
Genre: Angst, Anniversary, Claudia Stilinski Feels, First Time, Friendship/Love, Hale Family Feels, Humor, M/M, Sad
Language: English
Status: Completed
Published: 2021-03-19
Updated: 2021-03-19
Packaged: 2021-03-28 20:27:38
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,555
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30145140
Author URL: https://archiveofourown.org/users/AgentAlexKrycek/pseuds/AgentAlexKrycek
Summary: It's the day of the year that Stiles dreads more than anything. However, this time around he's taken steps to take his mind away from the anniversary of his mother's death. A certain Sourwolf's never gonna know what hit him! In my AU, the men are both of legal age. This is my second foray into the 'Teen Wolf' universe, but the very first semi-serious story. First Time, Fluffy Feels, Mother's Love & Loss, and some Angst. Humor.
Relationships: Derek Hale/Stiles Stilinski
Kudos: 17





	Momma's Boy

Momma's Boy by AgentAlexKrycek

A far as seductions went, Stiles couldn't help but feel this one was kinda lame. It wasn't that he didn't have it all planned out to the very last detail, in his opinion, all his preparations were spot on. He'd been obsessing about this for weeks, ever since he'd noticed the date on the calendar getting closer. So here he was, bare-assed naked on what passed for a bed in the old Hale house. He had let himself in, liking that term much better than breaking-and-entering. It was only fair, after all, considering how many nights Derek had just popped into his bedroom unannounced in the middle of the night. At least I used the door, he justified. The only thing missing was the guest of honor - one very absent and missing-in-action Sourwolf.

To pass the time, Stiles listened to his I-Phone, wondering just what type of music would be apropos for his official deflowering. Can guys be deflowered, he wondered in passing. There really should be a more butch term for it. He finally settled on Fun's "Some Nights" 'cause it had a beat you could really keep time to. He started second-guessing himself, wondering if he should go for a more subtle and romantic choice. Then triple-guessing himself, because if tonight was anything, subtle was not it! Nope, subtlety wasn't even in the right neighborhood. That was the final thought he had as he drifted off to sleep. That was one of the problems with Adderal, the high was great but the crash was hell. He wasn't sure how much time had passed, when he was awoken by a very masculine voice repeating his name.

"Stiles… Stiles…! Let's forget for a minute that you are in my house, ...uninvited. Is there a reason why you're bare-ass naked in my bed?" Derek asked, the mix of curiosity and amusement clearly evident in his tone.

"The better to be fucked by you, Wolfbutt." Stiles said groggily into the pillow. "Welcome home, by the way, and about damn time!"

Derek was clearly taken aback, which was rare for the intense young man. Not too many things surprised him, ever. But this, this left him at a complete loss for words. After making a few shocked mouth-movements reminiscent of a fish struggling for air. He calmly, at least he felt it was close to calmly, asked, "Are you drunk again, Stilinski?"

There was a long silence as Stiles gathered his thoughts. Finally he spoke, but what he had to say was not what Derek had ever expected to hear. " I'm so freakin' tired of being 'Stiles!' Of being the good son, the best friend, the one who's always there for everyone –every-damn-time." Derek could feel the conviction behind the words, and took a step forward from where he was leaning on the charred doorframe. "And, I'm sick to death of being the only virgin in our group!" Stiles spit the word out, almost like an expletive. "Everyone, and I mean everyone, is having sex except for me… And what's wrong with me, huh?! I'm not hideous. I'm funny, I'm smart as hell, I'm a good dancer, and a good listener… I'm a catch! I've got a good heart, but you know what that gets you in life? It gets you Saturday nights alone at home with the internet, wondering how much more abuse your poor little heart can take," Stiles confessed.

The role of comforter did not come easy for the lone wolf, but he tried the best he could. "There's nothing wrong with you Stiles, except you talk entirely too much, but that's neither here nor there. And, you're right. You are a catch. You're gonna make some lucky girl very happy someday. You're only eighteen, and then so only by a few months. You haven't had the chance to grow up yet, to explore, to become the person you are destined to be. You have college coming up soon, don't be in such a rush to grow up. It will all happen in its own time. You need to let that day happen naturally, so that it will be special. Besides, I thought you were in love with Lydia?"

"Oh please, that ship sailed a long time ago. ...Right into an iceberg, I might add. Total disaster ~ lots of people screaming, dying, and freezing. I know an impossible dream when I see it there, Don Quixote," Stiles snapped, mixing up his metaphors, but not his core meaning. "And what's with the 'after school special' advice there, Yoda?! There's only one thing I need from you, and it's in your pants! This isn't an open-ended offer… Well, I guess it kinda is..." Stiles giggled at his unintentional double entendre. "This is a one-time limited pass to ride the Stalinski train. Climb aboard, 'cause this train is leaving the station, destination ~ Ecstasy." He sang the last word, stretching it out for effect. Stiles wondered if he had gone too far that time, and further wondered why he hadn't been killed yet. He was certainly ready to die ~ of embarrassment. He decided to press his luck even further yet, "Where have you been anyway, while I've been here with my butt literally in the air waiting for you? Really, you never see the virgin sacrifice cooling her heels in all those old movies. I'm a valuable commodity here." Realizing the day and the late hour, he added, "Oh, crap, you haven't already gotten laid tonight have you?"

"Not that it's any of your concern, or business, but no I haven't had sex tonight. And, if you must know, I was at Scott's house where, by-the-way, we were discussing YOU. What the significance of today is, and the fact that you tend to go a 'little bat-shit crazy' this time of year." Derek carefully explained. Adding, under his breath, "Boy, you hit that nail on the head, McCall, and way-way-way undersold it!" The two had expected a panic attack, maybe an inebriated and plastered Stiles, or some other form of acting-out on this, the anniversary of Stiles' Mother's passing. Nothing could have prepared them for this though.

Stiles groaned into the pillow, and not in a sexy-times sexual way, wrapping it around his ears. "Uggggh, I'll take Scott McCall for the Cock-Block, Alex…"

"Will you please turn over and look at me, Stiles," Derek pleaded, finally making it to the foot of the bed and sitting on the tiniest fraction of mattress that would still allow for the support of his muscular frame. "As spectacular as your ass is, I'd really rather talk to your face." He regretted the attempt at levity as soon as he had said it. But, it had the desired effect and broken Stiles' melancholy mood.

"You really think my ass is spectacular?" Stiles cheerfully asked into the pillow.

"Yeah, I suppose as far as an other guy's ass goes, It's going to make someone very happy, someday," Derek replied, trying to save face. Derek wondered in passing if Stiles had waxed, then quickly shook his head to get the unwelcome thought out of his mind.

"I don't want to make someone happy, I want to make you happy. I want my first time to be you…," the younger man whined ~ but in a totally masculine way.

Derek gently rubbed the young man's back trying to comfort him, and trying to keep his hands as far from Stiles' ass as possible. "For the love of all that's Holy, will you Please roll over and look at me."

"I can't," Stiles said miserably.

"And why not?" Derek asked.

"Because I'm completely naked, that's why," Stiles answered.

"Umm, not sure of your logic there, since you've been naked this entire time…," Derek corrected.

"But not that naked… If I turn over, you'll be able to see all of me."

Derek almost told him that he had seen him naked several times since they had met. There was many an evening he had to abort a late night visitation after a cursory look through the bedroom window. Sometimes those looks had been more than fleeting, leaning towards longing. It wasn't creepy; it was his responsibility to keep an eye on his packmates. But now was definitely not the time or place for that conversation. "Well, we sure as hell can't continue like this! What can I do to help? The lights are off already; I guess I could wear a blindfold, if that would help. I can't believe you are this self-conscious. I mean you had gym and lacrosse, dozens of guys saw you naked everyday."

"Yeah, but they're not Derek-fucking-Hale! They're not fucking gorgeous and flawless."

Derek could not hold back his cocky smirk. "You think I'm gorgeous?" Derek gloated and goaded, eliciting a more miserable groan from below. "If it'll help, I can take my clothes off as well. But the boxers stay on, we should be prudent." Derek justifying the move in an effort to get slightly closer to going to bed, in what was after all, his own damn bed.

"Underwear too!" Stiles added hopefully.

"Umm, no. I keep the boxers on, and you keep the sheet –Deal?"

"Deal. Your cock's probably perfect too," Stiles berated. "Just like the rest of you."

"Yeah, and really big too! It would do you good to try to work up to me." Derek answered, without skipping a beat.

Groan. "You're totally loving this aren't you….," Stiles cursed up at him, before pitifully trying to dig himself deeper under the covers.

For the first time, Derek was able to see Stiles' intense golden brown eyes, and for the first time he saw the sadness that lay hidden just below the surface. He wondered why he had never noticed it before. He put his arm protectively around the younger man, mostly in an attempt to keep him from flipping all the way over again.

"I'm curious, Why me…? I mean, it's obvious you gave this some thought," Derek asked. Again, It took some time for the answer to present itself.

"Well, Scott is out of the question, completely! We've been best friends forever, almost family, really. You know he's like my brother and just, uggh! (full body shudder) I'm not willing to sacrifice that. Jackson is pretty, but way way too into himself. You don't want your first time to be with someone who yells out his own name when he cums! Also, I'm trying to quit Lydia cold-turkey. I figure sleeping with her boyfriend would not fit with that! I mean the entire time, I'd be thinking about were his cock had been, eeeeewww! Danny was a possibility, but I didn't want to be a home wrecker. Doesn't he have a boyfriend already? With Boyd, you have that whole 'never go back thing,' and I didn't wanna risk it. Since I haven't had any sex yet, I wouldn't want to limit my options for later. And so that left Isaac ~ hot damaged orphan Isaac. I seriously considered him. I mean have you seen him? He's kinda dreamy with that gorgeous blond hair and those blue eyes. And his heart is so good…"

"Uhhm!" Derek punctuated, trying to get Stiles back on track ~ any track.

"Sorry. But, I kinda figured we're both bottoms so that wouldn't ever work! I want my first time to be with a man. A real man, an alpha-male if you will. Hence you."

"Your first time should be with someone like Isaac," Derek stated matter-of-factly. "Someone that's capable of giving you all the love you deserve. Not me, I'm too broken. Too damaged. Too long alone." For a while the silence was deafening.

"So how long have you known you were gay?" Derek asked.

"I'm not sure if I am or not," Stiles answered. "Hard to put a label on a can that hasn't been opened... But my luck with women is only secondly bad to yours. I mean, my girlfriends have never tortured me, used me, then viciously murdered my entire family….Oh, Holy God, I'm sorry Der! I don't think before I talk, sometimes. I didn't mean that like it sounded; as bad as it sounded, I mean…I'm so Sorry, Dude. So shutting up now!"

Derek let the hurtful comment pass; Stiles did have a point. There was a long pause, where nothing was said.

"I miss my Mom, Der." And there it was. Finally. The other shoe had dropped, and Derek felt like it hit him right between the eyes.

"Me too. Not a single day ever goes by I don't think of, or miss, my family," Derek let his fingers run through Stiles' buzz cut hair, loving the way the stubble felt under his touch. He could smell the tears before they even started.

And once they began, they racked the younger man's body. Like a dam breaking, years of bottled-up sorrow spilled out. Derek felt his own barriers crumbling, feeling as his face became wet as well. His grip on the other man tightened. He braced himself, telling himself he had to stay in control. "You're the only one who knows, Derek. Really knows... You're the only one who can truly understand. You're the only one who has been through this… I feel so alone, all the time. There are times I wish it had been me instead…"

"Don't you ever say that again, Stiles!" Derek hadn't even realized he had been kissing Stiles' neck and shoulders for quite some time.

Stiles purred, as his eyelids grew heavy. "That feels so good. Don't stop."

Derek pulled him even closer, spooning him as they fell asleep together.

The last conscious thought Stiles had was, "Hey, what happened to your boxers?"

"I always sleep nude, it's a wolf thing." Derek explained sleepily. "But that changes nothing, because nothing is gonna happen tonight, so quit fidgeting."

"I'm just saying it's a real shame to waste an incredible hard-on like that," Stiles propositioned.

"Stiles, don't make me carry you out to that heap you call a vehicle," Derek warned.

~Hours Later~

Stiles woke suddenly, in a panic, several hours later. "Derek! Derek, wake up! Dude, I'm pretty sure your cock's inside me!"

"Oh god, oh God! How the hell did this happen!? Hold on, I'm pulling out," Derek yelled.

Stiles grabbed his arms in a death grip and calmly stated, "If you dare move a muscle, I'm gonna rip your throat out with my teeth! Let's discuss this calmly…. As I see it ~ mission accomplished. There are no longer any virgins in this bed. Wait, do you have to cum, for it to qualify? No, I guess not. Kinda wanted to be awake when it happened though …But, I don't think we should waste this. I'll never, ever have another first time."

Derek was still in shock, his mind was reeling from all the permutations this would cause, and from the overwhelming sensations being telegraphed from his cock to his brain. "How the hell did this even happen? It's your fault, you know, if you hadn't been rubbing all up against me like that, and God why do I smell cinnamon? Where the hell is that coming from? That's it, I'm officially losing my mind... or having some kind of aneurysm."

"Sorry Sourwolf, it's the lube. It's scented and flavored. I was trying to cover all my bases," Stiles explained. "I had prepared myself before you got here. I just wanted to be prepared for anything and everything."

"Oh my God, what are you a Boy Scout? Don't answer that! And stop doing that with your muscles right now! Are you positively sure you're a virgin?!"

"Relax, will you. I'm just trying to get used to the feeling. From all I've read, I thought it would be much worse. You feel really good, kinda silky even." Stiles purred.

"That's because the only thing in you at the moment is my head, there's still a long, long way left to go," Derek corrected. To drive his point home, he let himself slide-in a few more inches.

"Oh my God!" Stiles yelped. "Pull it out, pull it out! I've changed my mind. Holy God! Is that thing even completely human?"

Derek attempted to distract him by taking small bites of his shoulder and neck. "Let's give this a few more minutes and a few more inches… Like you said, we'll never get a second chance at our first time." He lovingly stroked Stiles sweat-soaked hair. "You're in charge, you set the pace. Whenever you're ready… And remember, we can always stop if you need to."

"Derek, don't take this the wrong way, but shut up and start fucking me." Stiles stated.

Hours later, the two new lovers lay entwined in each other's arms, drowning in the afterglow. The bed was completely wrecked, and the two were still covered in sweat. It was the best exhaustion they had ever felt. That's why it came as such a shock when Derek felt Stiles start to cry again. And this time, the sobs were even harder than they'd been earlier.

"Babe, what's wrong? Are you okay? What can I do? I didn't hurt you did I," Derek's eyes searched the other man's tear-filled eyes.

"I'm okay, really," Stiles lied, crying even harder still.

"Do I seriously need to pull the I-Can-Hear-Your-Heartbeat card, Stiles?" Derek asked concerned. "Rule one, we never keep any secrets from each other, or tell a lie to protect the other's feelings."

"You're right. I'm sorry. I was just thinking about my Mom, and how much I think she would have loved you," Stiles said, getting himself under some control.

Derek pulled him in even tighter. The same thought had been going through his own mind as well. He was quiet for quite a while, then offered, "You know Stiles, this no longer has to be such a sad anniversary. I mean, after tonight, and us, I mean. I'm not saying this to take away anything from what this day means to you, but you no longer have to just be so sad on this day, from now on. It's the day we got together, finally. It can kind of be our unofficial anniversary, until there's a more permanent one."

"My Mom, would have liked that." Stiles said. "She hated for anyone to be sad. Whenever I had a bad day at school, or Dad had a bad day at work, we'd come home and the house would smell amazing! There'd be cakes or cookies, and hugs and kisses. She could always make everything better. "Hey, wait a minute, did you just mention long-term plans?! What the hell happened to me experiencing all life has to offer, and all that other dumb stuff?!"

"Well, all that was before you made my wolf pick you," Derek quipped. "You said it before, once you've had Derek 'fucking' Hale, you no longer have any need to roam or explore, little Pup.

"You're pretty damn full of yourself there, Hale." Stiles commented dryly.

"Not as full as you were of me, just a few minutes ago," Derek snorted, happy to get the last word for once.

"Um, case-in-point, I was sound asleep for the majority of it…" Stiles fired back. The tiny nudge Derek gave him almost sent him tumbling from the bed. Derek pulled Stiles back to him.

"Now you're stuck with us, Stiles. Where you go, I will go, to the ends-of-the-Earth, 'til death do we part. You okay with that, Mate?"

"I didn't know you were Australian Derek," Stiles giggled into the bigger man's chest. "Wanna go pound a Foster?!"

"I'm not Australian, what makes you think…" Derek asked totally confused.

"Gotcha, Mate."

"Yes you do, Stiles, always." Derek kissed his lover quiet. "Hey, who's this Foster? Is that one of your friends or teammates? Because, I'll have you know, I don't play well with others, I don't share, and I don't do three ways! You didn't mean Isaac did you? Because he's really much more of an orphan than a foster kid…"

"I waste my very best materiel on you," Stiles said, shaking his head.

"Gotcha!"

~The End~

Note: This story was originally published in June of 2013. This started as a chapter in another story, then gathered a life all it's own. It was my most popular story on Fan Fiction for the longest time with tens of thousands of hits. So, I'm posting it as a stand-alone. Thank you for reading. Please be kind and constructive. I don't own anything Teen Wolf myself, but worship Jeff Davis for bringing these two characters into my life! Season One/Early Two timeframe. Please Review and Fav if you like it. No Haters Please! If you don't like same-sex love stories, don't read. Simple. I live to hear from you guys! I just want to take this chance to Thank all of you beautiful readers. I have been touched by your comments, reviews, and private messages. You are all so amazing! I cannot tell you what your time and words have meant to me. I am blown-away, my other Teen Wolf story "Car Problems" has had such a great response worldwide. I only hope that this one is embraced as warmly by a fraction of that number. Peace & Love, always, Alex.


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